Facile and efficient synthesis of 1-haloalkynes via DBU-mediated reaction of terminal alkynes and N-haloimides under mild conditions

被引：40

作者：

Li, Mengru ^{[1
]}

Li, Yueju ^{[1
]}

Zhao, Baozhong ^{[1
]}

Liang, Fushun ^{[1
]}

Jin, Long-Yi ^{[2
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

[2] Yanbian Univ, Fac Chem, Yanji 133002, Peoples R China

来源：

RSC ADVANCES | 2014年 / 4卷 / 57期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; COMBINATION; BROMINATION; IODINATION; ACCESS; CARBON; POLY(DIIODODIACETYLENE); BROMOALKYNES; ACETYLENES; ALKENES;

D O I：

10.1039/c4ra04736b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Directly from terminal alkynes and with N-halosuccinimides (halo = Br and I) or N-cholorophthalimide as the halogen sources, DBU as the activator, 1-haloalkynes were prepared in good to excellent yields at room temperature. Bis(bromoalkyne) and bis(iodoalkyne) were also synthesized in excellent yields with the NBS(NIS)/DBU combination. The reaction features inexpensive and readily available reagents, mild conditions, simple execution, extremely short reaction time, broad halogen scope, high efficiency and is metal-free. Compared to the literature reported methods, our synthetic strategy provided a greener approach towards 1-haloalkynes.

引用

页码：30046 / 30049

页数：4

共 50 条

[1] Efficient synthesis of 1-iodoalkynes via Al2O3 mediated reaction of terminal alkynes and N-iodosuccinimide
Yao, Ming
Zhang, Jingjing
Yang, Sen
Xiong, Hangxing
Li, Li
Liu, E.
Shi, Hong
RSC ADVANCES, 2020, 10 (07) : 3946 - 3950
[2] A facile copper(I)-catalyzed homocoupling of terminal alkynes to 1,3-diynes with diaziridinone under mild conditions
Zhu, Yingguang
Shi, Yian
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (43) : 7451 - 7454
[3] 1,2-Dibromoalkanes into alkynes by elimination reaction under DBU conditions and their application to total synthesis of sapinofuranone B
Kutsumura, Noriki
Yokoyama, Tadashi
Ohgiya, Tadaaki
Nishiyama, Shigeru
TETRAHEDRON LETTERS, 2006, 47 (25) : 4133 - 4136
[4] DBU/DMSO PROMOTED DEHYDROBROMINATION OF 1,1-DIBROMOOLEFINS - A GENERAL-SYNTHESIS OF 1-BROMOAROMATIC ALKYNES UNDER MILD CONDITIONS
RATOVELOMANANA, V
ROLLIN, Y
GEBEHENNE, C
GOSMINI, C
PERICHON, J
TETRAHEDRON LETTERS, 1994, 35 (27) : 4777 - 4780
[5] Cu-catalyzed transannulation reaction of pyridotriazoles with terminal alkynes under aerobic conditions: efficient synthesis of indolizines
Helan, V.
Gulevich, A. V.
Gevorgyan, V.
CHEMICAL SCIENCE, 2015, 6 (03) : 1928 - 1931
[6] Efficient synthesis of 1-adamantanecarboxaldehyde by the GaCl3-mediated carbonylation of adamantane under mild reaction conditions
Oshita, M
Chatani, N
ORGANIC LETTERS, 2004, 6 (23) : 4323 - 4325
[7] Facile synthesis of C-terminal peptide thioacids under mild conditions from N-sulfanylethylanilide peptides
Shimizu, Tatsuhiko
Miyajima, Rin
Sato, Kohei
Sakamoto, Ken
Naruse, Naoto
Kita, Miku
Shigenaga, Akira
Otaka, Akira
TETRAHEDRON, 2016, 72 (07) : 992 - 998
[8] Efficient, Mild and One Pot Synthesis of N,N′-Bis(salicylidene)arylmethanediamines via Three Component Reaction under Solvent Free Conditions
Naeimi, Hossein
Rabiei, Khadijeh
Salimi, Fariba
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (12) : 2445 - 2448
[9] Efficient and rapid synthesis of N-substituted isoquinolin-1-ones under mild conditions: Facile access to doryanine derivatives
Takwale, Akshay D.
Jeon, Yeong Uk
Lee, Dong Ho
Kim, Hyun Jin
Hwang, Jong Yeon
TETRAHEDRON LETTERS, 2019, 60 (18) : 1259 - 1261
[10] Synthesis of Ynones via N-Iodosuccinimide-Mediated Oxidation of Propargyl Alcohols under Mild Conditions
Qi, Hongbo
Xu, Shuai
Zhao, Ruiguo
Chen, Shufeng
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21): : 13726 - 13733

← 1 2 3 4 5 →